Ethanol → HCID 54309330, compound

Participants

Reaction Steps

1,3-Dioxo-6-(phenylthio)-1H-benz[de]isoquinoline-2(3H)-acetic acid (3.55 g, 9.77 mmoles; described in Example 1), anhydrous pure ethanol (12 ml), toluene (30 ml) and p-toluenesulfonic acid hydrate (0.2 g) were heated at reflux for 16 hr in a Soxhlet apparatus in which the thimble was filled with hydrated alkali-aluminium silicate (3 A Molecular Sieves). The resulting clear mixture was washed with water (2×80 ml), 5% sodium bicarbonate (2×80 ml) and brine (100 ml), dried (MgSO4) and concentrated to dryness. The residue was crystallized from isopropyl ether-carbon tetrachloride (1:1, 60 ml) to give 2.85 g of the title compound; mp 132°-134° C.; UV (MeOH) 231 and 344 nm, ε=25,170 and 7,360 respectively; IR (CHCl3) 1743, 1695 and 1660 cm-1 ; NMR (CDCl3) δ1.25 (t, 3H, J=7 Hz), 4.15 (q, 2H, J=7 Hz), 4.85 (s, 2H), 7.15-8.65 (m, 10H); Anal. Calc'd.: C, 67.50%; H, 4.38%; N, 3.58%; Found: C, 67.87%; H, 4.44%; N, 3.50%.

Provenance & Evidence